4-Nitrobenzyl chloride → HCID 18315897, compound

HRID 275746Notes

Reaction equation

HRID 275746 reaction equation
Cl.[CH2:2]1[C:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[O:10][C:6]=2[CH2:5][CH2:4][NH:3]1.Cl[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>CC(C)CC(=O)C.[I-].[K+]>[N+:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:3]2[CH2:4][CH2:5][C:6]3[O:10][C:9]4[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=4[C:7]=3[CH2:2]2)=[CH:18][CH:19]=1)([O-:25])=[O:24]

Participants

6

Reactant 3

HCID 74824-Nitrobenzyl chlorideHCID 10340Sodium CarbonateHCID 124995131,2,3,4-Tetrahydrobenzo-furo[3,2-c]pyridine hydrochloride

Product 1

HCID 18315897HCID 18315897, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (1:1), (0.05 mol), 1-(chloromethyl)-4-nitrobenzene (0.05 mol), Na2CO3 (7 g) and potassium iodide (0.1 g) in 4-methyl-2-pentanone (250 ml) was stirred and refluxed for 8 hours. The mixture was allowed to cool to room temperature. The reaction mixture was filtered and the filtrate was evaporated. The oily residue was dissolved in CH3CN/diisopropyl ether and stirred. The precipitate was filtered off and dried, yielding 8 g of 1,2,3,4-tetrahydro-2-[(4-nitrophenyl)methyl]benzofuro[3,2-c]pyridine (intern. 11). The filtrate was stirred with HCl/2-propanol. The precipitate was filtered off and dried, yielding 9 g of 1,2,3,4-tetrahydro-2-[(4-nitrophenyl)methyl]benzofuro[3,2-c]pyridine hydrochloride (.HCl) (interm. 12).

Workup

  1. temperaturerefluxed for 8 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated
  4. dissolutionThe oily residue was dissolved in CH3CN/diisopropyl ether
  5. stirringstirred
  6. filtrationThe precipitate was filtered off
  7. customdried

Sources & evidence

ORD record
ord-247142edf322417da4c1dfbf1202c268
Source dataset
uspto-grants-2002_03
Patent number
US06352999B1

Reaction notes

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